5th Time’s a Charm. Happy Birthday to Us

This week, theSkimm turns five years old. That is a BFD for a lot of reasons. Most startups do not make it this far. 90% actually fail. And of those 10% that survive, only 50% make it to the 5-year mark. And we are here. We are still standing.

Sometimes amidst the craziness, it’s easy to feel too busy to celebrate, or to think about the glass as half full, when you look at all that still has to get done.

But this week is about us taking a moment and saying: We are really proud of ourselves and theSkimm. We’ll get into why in a bit. First…

Here are 5 things we once thought were insurmountable:

1. Raising money

We are two of the most stereotypical liberal arts students there ever were. No Excel knowledge. No savings. And no understanding of what any of the Silicon Valley jargon meant. But we taught ourselves. We became expert networkers and left every meeting — even the terrible ones — with an introduction to someone else. What we ended up with was a spreadsheet of hundreds of names in red of those who rejected us, but also hundreds of people to stay in touch with until that red turned to green. Green meant money. And money meant team.

2. Staying focused

Realizing the wealth of opportunities thrown our way has been one of the most exciting things over the past few years. We’ve been offered international expansion, our own network show, our own book, a clothing line, a coffee line, and a wine line. We’ve been told to get more products out more quickly. Once we got past the, ‘Omg this is so exciting’ part to the, ‘Omg how does Ryan Seacrest do all of this’ part, all we heard and saw were, ‘Distraction. distraction. distraction. distraction.’ Learning how to focus allowed us to do two things: 1. Establish and stay true to our mission that theSkimm makes it easier to live a smarter life, and 2. Hunker down and focus systematically at growing our base and then activating our base. We became experts at saying no, and then taught ourselves how to start saying yes.

3. Hiring the right team

Someone once told us, ‘Hire slowly, fire quickly.’ When we were just starting out, we misunderstood what that meant. We hired way too slowly and parted ways with employees too slowly as well. In the 3.5 years we have had a team, we have learned so much about who we are as individuals. We have learned how to become stronger communicators: how to ask for what we want, how to explain why we’re disappointed, how to say things so they are not taken the wrong way. We’ve also learned that it’s painful on both sides when things don’t work out — something we never ever thought about in our previous careers. We would let fear of what this would do to company culture and workload paralyze us, and we sometimes waited way too long to part ways with someone. Which doesn’t help anyone.

4. Making mistakes

The truth is we hate making them. We are both Type A people and tend to hire other Type A people. Making mistakes is our least favorite thing ever…and at times the fear of that set us into analysis paralysis. Launching Skimm Ahead took us a year when it should have taken six months because we were so scared to mess up. We have lost candidates because we took too long to decide if they were the right person. We’ve lost investors because we took too long to wonder if this was the ‘right’ deal. We’ve had to learn to let go and show our team that it’s ok for them to fail too. Now each week we appoint someone who is the failure of the week — meaning they tried something new, it didn’t work out, and we want to celebrate that they tried. And then they get to wear a hard hat that says ‘fail so hard.’ So that’s fun.

5. Being bigger

For many years we liked to joke that we were the little engine that could. Being the big train terrified us and didn’t feel like it was ours to be. For each milestone fundraise, we would set small rewards for ourselves. Seed raise was a nice haircut, Series A was a small shopping spree to Club Monaco, Series B was a fancy wallet. The next milestone is a fancy, grown-up purse. We recently told a mentor this, and she said, ‘Girls, dream bigger!’ And she was right. Sometimes we have been too scared and superstitious to realize how big of a company we have built — both in size and in value. We have chosen too small office spaces time and time again because we were scared we wouldn’t grow into something bigger. We still sometimes pitch ourselves as ‘the newsletter company’ because we are scared to say, ‘We created a huge media empire.’

But at age 5, we are happy to say, ‘Hi, our names are Skimm A and Skimm B, and we hired an all-star team that is building something f*ing huge.’

This is what we’ve done:

We have built a robust subscription business with premium offerings that is changing how information integrates into the daily routines of its consumers

We have built a one-of-a-kind Skimm’bassador community that is 25,000+ people strong and brings in 20% of our annual growth

3 former first families Skimm, Oprah Skimms, every newsmaker we ever idolized growing up Skimms

We registered more than 110,000 people to vote. Meaning theSkimm registered proportionately more people to vote than Facebook by more than double

We have raised over $15M in venture funding on our own

We launched an audio/video arm called Skimm Studios

We launched a data arm called Skimm Studies

We move product. We are one of the top ways to sell books to this audience. And have changed the trajectory of so many businesses that have worked with us

We are the only information company that can say their audience doesn’t just vote one way. We launched a marketing platform called No Excuses to connect Skimm’rs on both sides of the aisle around issues driving the national conversation

We have built an all-star team

We have hired our first exec team (more on that later)

We’ve ignored a lot of [insert expletive here] who told us that this was a bad idea, that we couldn’t do it on our own, or that our idea wasn’t big enough

And we have learned to brag. Because if you don’t do it for yourself, no one else will

All of the above has come through blood (seriously, we are both clumsy), sweat (so much sweating), tears, and mistakes. So many mistakes. So thank you to all of our advisors, investors, friends of the company, and mentors who have picked up the phone when we called nonstop and answered our frantic texts. And of course, thanks to our parents, families, and lifelong friends. Seriously, we’d be nowhere without your support.

Speaking of being nowhere…we’d be nowhere without our team. The work ethic, the passion for this company and its community, the weirdness, and the ability to laugh at the absurd along the way, inspire and humble us every day. Thank you for believing in us before we had any of the fancy stats, and thank you for genuinely being good people. We are honored to work with you. And we really like you. A lot.

So in taking this moment to celebrate, it’s surreal to look back at the milestones that we once thought were insurmountable. But we got through.